Sigmatropic rearrangements and related processes constitute a very useful class of reactions in organic synthesis. The overall goal of this research is to explore the scope and mechanism of alkoxide induced (1,3) shifts and the synthetic consequences of such reactions. Often such transformations make readily available molecules uniquely suited for new applications and new methodology for the construction of biologically important molecules. Although the primary goal is to learn all we can about the reactions in question rather than to pursue total synthesis, the reactions will be investigated in the context of antibiotic and cytotoxic terpenoids, macrolides, steroids, and prostaglandins. These methods provide great latitude for structural modification and should be useful for the synthesis of many biologically active compounds.